We have our own barn. I have never boarded, so I don't have that to compare to. Really the only drawbacks I've found are the lack of indoor arena (though plenty of boarding facilities don't have that either) and the never day a day off thing. Even if we are all sick, we can't say "Oh, I'm just not going to go to the barn today.."
We have a WONDERFUL petsitter who takes care of our animals when we go on vacation. The horses are no problem for her. We do have to send our german shepherd to a kennel, because he won't let her in the house lol. Our horses are very easy to take care of though. Our barn is set up with doors that open from the stalls to the paddock/pasture. We leave the doors open so that the horses can come and go as they please. Stalls don't get that dirty very quickly since they are never shut in their stalls (unless waiting for the farrier, vet etc) and none of them have any major special needs, so the petsitter really just has to feed and water them.